


The Zimmermann Charm

by nonnymouse



Category: Check Please! (Webcomic)
Genre: Alternate Universe - Prostitution, Loss of Virginity, M/M, Rimming
Language: English
Status: Completed
Published: 2018-05-09
Updated: 2018-05-09
Packaged: 2019-05-04 07:21:52
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 1,495
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/14587917
Author URL: https://archiveofourown.org/users/nonnymouse/pseuds/nonnymouse
Summary: Jack is a hooker. He's better at it than you'd expect.Bitty is trying to lose his virginity. He's as bad at it as you'd expect.





	The Zimmermann Charm

**Author's Note:**

> Written for this kinkmeme prompt:
> 
> "Hooker!Jack AU, Jack/any
> 
> Jack's a hardworking hooker determined to amass enough money to retire comfortably. The SMH are his clients.
> 
> (Is he down on his luck and blowing Holster in the alley behind an NHL practice facility? Prosperous and tenderly initiating Bitty to the world of sex? ANY/ALL/BOTH/WHATEVER)"
> 
> https://omgkinkplease.dreamwidth.org/586.html?thread=227146

Jack’s clients mostly fit into one of two categories: creepy old men or frat guys, who could be considered creepy young men. The guys on the Samwell hockey team were better than most; they sometimes got weird about getting their dick sucked by a dude, but they didn’t get violent.

It was why he agreed to a two-hour session with one of the freshman on the team, sight unseen, when one of the upperclassmen sent him a text. Of course, it had to turn out that his client wasn’t another big, horny jock, but a sweet little closeted gay kid who wanted to lose his virginity.

The good thing about creeps was that they didn’t care about Jack’s personality. Virgins, on the other hand, wanted romance. He’d already bruised this guy’s feelings, he could tell. He did not go on a house call to not get paid.

"Lordy, I don’t even know what I was thinking," the kid was saying in an increasingly thick accent, "I’m gonna lose my scholarship because I can’t get over this fear of physical contact thing and I somehow thought if I could do this I could at least be good at the gay thing."

Offering comfort wasn’t Jack’s strong suit, so he focused on what he was good at. He grabbed the kid, heavier than he expected, carried him to the bed, and planted him so he was ass up on the blue cotton sheets. "I can do physical contact," he said, pulling down the little shorts that covered a nice, round ass. That was another plus to the hockey guys, for an ass man like Jack.

He dived right in, holding the kid’s cheeks open and licking his tight hole, coaxing it open. The kid cried out in surprise beneath him, one foot kicking out reflexively, but soon he was melting beneath Jack, panting with soft, pleased surprise. "Oh, my goodness," he gasped, and Jack was pretty sure those were strong words coming from this kid. It was rather adorable, especially given that boys who were actually that innocent didn’t hire hookers. There was someone tougher and wilder ready to climb out of that big-eyed, non-threatening shell.

While he kept up his attentions with his tongue and mouth, he quickly rolled on a condom so it had time to warm up and his cock would be back in business by the time it was needed. Then he got his hands back into play, adding a few fingers to the mix, pushing lube deep into the kid’s hole, alternating with the licks. The lube didn’t taste that great, but a virgin would need it and the kid didn’t need to know.

"What position do you want to do this in?" Jack asked him when he thought the kid would shoot if he kept licking him any longer. "Doggy, face-to-face, spooning? Other?"

The kid laid limp on the bed, face down, still trembling from the pleasure of being eaten out by an expert. "I, uh, I don’t know? Which one is most popular?"

"Well, most guys want to fuck me rather than get fucked, so I don’t have the most representative sample. Doggy’s always popular." He didn’t add that the kid probably wanted the romance of face-to-face rather than getting treated like a hooker, but Jack wasn’t a romance guy any more than he was comforting. He was decent at making a big gesture, when necessary, but the kid was not a boyfriend. Which meant less personal was Jack's own preference.

"Okay, then," the kid agreed.

Jack helped him get into position, telling him, "About like you were. Rest your head in your hands … that’s good, just make sure you’re comfortable."

But once he had him in place, he didn’t wait. He traced the curve of one hip, figuring out where to hold on, then guided his cock in. The kid’s hole practically sucked the head of his cock in, although he was tight enough that the rest took more work, rocking himself back and forth as the kid’s body relaxed and let him in deeper. "Oh, oh, oh," the kid was gasping, as if he thought a little penetration meant they’d already reached the main event.

Jack was in, sheathed to the hilt in that tight little body, which meant he had to show the kid the real joy of sex. With his left hand, he reached down and stroked the kid’s cock, finding the rhythm he wanted. Then he started thrusting in time with his hand, testing how hard the kid wanted it. Gentle thrusts didn’t seem to do too much for him, but his cock practically leapt out of Jack’s hand when Jack thrust hard enough to make the kid push back against him to keep his balance.

So rough it was. He really needed to find more clients who liked to take it, because thrusting into a hot jock who was whimpering like he’d die if he didn’t get more cock was the best time Jack had while on the clock in ages. The kid was starved for it. It was a shame he had a virgin’s stamina, shooting while Jack was only warming up. Didn’t matter; the kid booked two hours, so Jack would get paid for two hours.

However, when Jack was tying off the condom and throwing it into the trash can the kid had so helpfully put right by the bed, the kid kept sneaking looks at his still-hard cock. "I want …" he trailed off, but Jack knew what those searing glances meant.

"That’s okay," he said, putting on a new condom. "That’s a popular request too."

The kid sank off the bed, as if the floor was magnetic and had pulled him down to where he belonged. He looked good there, glowing a little from the sweat dotting his skin. He swayed forward between Jack’s knees as if he was entranced, reaching up to touch Jack’s cock like he needed to assure himself that it was real and not a dream. It wasn't usual to get an ego boost from an appointment, but this was doing it for Jack.

Satisfied with what he found, the kid leaned in those last few inches and licked the tip. He grimaced at the taste of the latex; Jack should’ve packed flavored condoms, or at least flavored lube. But it didn’t stop the kid, thankfully. He opened his mouth and took more, even swallowing to push himself down another inch. He backed off, taking a moment to breathe, and Jack stroked his hair. "You’re doing good," he said.

It seemed the kid took it as a challenge, getting himself back on that cock and going for the goal. He kept those big brown eyes trained on Jack, and Jack kept his hand in his hair, guiding him. "That’s right, keep sucking. Throw in some licks too, show me that you can do it all. You’ve got a great mouth kid, tight and hot like that sweet ass. Yeah, get it down your throat. Just keep swallowing, you can do it. Don’t gag; fight the reflex. Tell your body what your brain knows, that you were born to take cock down your throat."

Jack couldn’t help it. He was the kid’s first after all, and it was easy to be complimentary about the blowjob when those pretty eyes were watching his every move, tearing up at the corners. So big and dark, he could read anything into those eyes. He looked as sweet as a gay kid could with a big cock in his mouth. He even smiled around it when he felt Jack come, even though Jack clenched his fingers and ripped out a few strands of hair.

"Not bad," he complimented the kid, used to having to catch his breath quickly. "But let me tell you, don’t become a hooker if you lose that scholarship. The nasty fuckers would latch right onto a little thing like you."

"Thanks, I think," the kid said as he stood up. His smile was uncertain, which happened to a lot of guys when it hit them that they'd just fucked a hooker, but he still looked more relaxed than at the beginning of the appointment. He'd been wound tight enough to snap, but a good rimming session always took care of that. "Let me get your money." He returned with an envelope, and a plate of cookies. Not a good a tip as cash, but Jack would take it.

"Feel free to call me again. I can always make time for an easy client."

The kid blushed as he walked Jack out. Jack didn’t bother clarifying that he’d meant easy on himself. He rather suspected that the kid needed someone to treat him like a sexy little slut. If he had someone like that in his life, they’d have already taken care of that pesky virginity. But Jack had been happy to do the honors, for a fee.


End file.
